Berlin 2015 – scientific programme

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O: Fachverband Oberflächenphysik

O 41: Inorganic/Organic Interfaces

O 41.29: Poster

Tuesday, March 17, 2015, 18:15–21:00, Poster B

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism — Joscha Vollmeyer, Friederike Eberhagen, Sigurd Höger, and •Stefan-Sven Jester — Rheinische Friedrich-Wilhelms-Universität Bonn, Kekué-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany

Three shape-persistent naphthylene-phenylene-acetylene macrocycles of identical backbone structures and extraannular substitution patterns but different (empty, apolar, polar) nanopore fillings are self-assembled at the solid/liquid interface of graphite (HOPG) and 1,2,4-trichlorobenzene. Submolecularly resolved images of the resulting two-dimensional crystalline monolayer patterns are obtained by scanning tunneling microscopy. A concentration-dependent conformational polymorphism is found, and open and more dense packing motifs are observed. For all three compounds alike lattice parameters are found, therefore the intermolecular macrocycle distances are mainly determined by their size and symmetry. This is an excellent example that the graphite acts as a template for the macrocycle organization independent from their specific interior. [1] J. Vollmeyer, F. Eberhagen, S. Höger, S.-S. Jester Beilstein J. Org. Chem. 2014, 10, 2774.